Episode 1

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Published on:

29th Jul 2025

001: Is Entrepreneurship Right for You? Here’s How to Know

So you want to be an entrepreneur—but you’re not sure if you’re cut out for it?

In this episode, Charles (a CPA who left corporate America to launch his own firm) and Seth (an Oxford PhD in business strategy who’s helped thousands start companies) break down the real traits, skills, and mindsets it takes to succeed as an entrepreneur—no fluff, no hype, no hustle culture.

You’ll learn:

  • What age group really succeeds in entrepreneurship (it’s not who you think)
  • The 3 key ingredients that matter more than personality
  • How to shortcut expertise and still deliver real value
  • What financial slack means—and how to calculate your personal runway
  • Why you don’t need to be extroverted, high-energy, or a sales ninja to succeed
  • What kind of goals actually lead to the lifestyle you want

Whether you’re a millennial figuring out your next move or a mid-career professional eyeing freedom, this episode gives you the clarity and confidence to take your next step.

🔗 Subscribe, rate, and review if you’re ready to build freedom—without the BS.

Got questions for Charles and Seth? Submit them HERE.

Transcript
Charles (:

to the Unsexy Entrepreneur podcast. We're so glad to have you. If you're a millennial who's trying to start their business, acquire a business, or grow their business, this is the place for you. No motivation, no hype.

Seth Jenson (:

We'll take you if you're

not a millennial as well, to be clear. You know, if you're old and this is your fourth act career, or if you're a teenager, we can help you. But yeah, as millennials, we see a need for millennials to get the support.

Charles (:

We do. boy. And I think today we're going to talk on, on a lot about what entrepreneurship is and if it's right for you. think, we're to talk about why I wanted to focus on millennials. obviously this can be helpful for everyone. but that's, we're going to talk about entrepreneurship, if it's right for you and if you should do it yourself. So Seth, think you've worked with more starting entrepreneurs than.

just about anyone in the nation. There might be a few people that have beaten you on that, but not many. How do you know if entrepreneurship is right for you?

Seth Jenson (:

Yeah, luckily those people probably aren't listening to our podcast. So they won't, they won't call us out on that. So yeah, I'll accept that. I've worked with the most entrepreneurs of anybody. the, yeah, so the research shows, that most successful entrepreneurs tend to be in their forties and fifties.

Charles (:

Hahaha

Seth Jenson (:

The reason we think that is, is because they've had decades to kind of develop industry experience and see opportunities and say, Hey, you know, my field is, you know, for take you as an example, I'm an accountant. I've been an accountant for 20 years or whatever it is. And now I see this innovation of I can, Hey, improve the accounting process or serve these clients a little better. So I'm going to spin off my own and kind of bring that to life. So that's kind of the typical entrepreneurial path. one that, that, that, the one that tends to be the most successful.

Charles (:

Can

you do it if you're in your 20s or in your 30s?

Seth Jenson (:

for sure. Yeah. mean, people, that's the beauty of it, right? And there's different industry differences as well. Tech, for example, skews young. Those founders tend to just be younger by nature because there's low kind of...

Charles (:

Mm.

Seth Jenson (:

A tech business is not as capital intensive. A lot of the time you can tinker and, and, and start something small and it can grow big. There's also a financial structure to support it through VCs and angels. So yeah, there's definitely exceptions to the rule. That's just kind of the, the, the cohort that consistently is the easiest to bet on, and taking the plunge. And I think there's kind of like three main reasons that those forties and fifties are sweet spots. And so if you can.

have these three things in your life and not in your 40s and 50s, you're good to go. There's nothing magical about being in your 40s 50s, but they tend to have expertise, like I mentioned, they've got some financial slack, so they've got the risk tolerance, know, they've got a nest egg or something that doesn't feel as scary of not having revenue for 12 months or 24. And then they've also built up a network along their career so they can have clients a little bit quicker. ⁓ So I think that helps.

Charles (:

Yeah. So one of my clients

that I originally thought of when you, when you said that, he runs a, a very specific type of marketing company and he was probably. Boy, I'm going to guess his age. Cause I don't know when he started his, his company exactly, but it was probably in mid forties to early fifties. and his company that he was working for merged with another company. He didn't like his boss.

He was just like, well, why can't I do this exact same thing on my own? He went out on his own. He already had all the clients. basically took half of his clients with him, suddenly had a great network going. and it was a pretty safe jump, right? ⁓ and yeah.

Seth Jenson (:

Mm-hmm.

Yeah. I think we'll end up talking about

that more in other podcasts, but those relationships are gold, right? And so again, it's a lot easier to start a business if you already know a bunch of the people that you'd want to invite as customers or work with as suppliers or partners, whatever it might be. Social capital, you know, is what is kind of the fancy term for that, but it makes a huge difference. And it just, you tend to have more of it the older you are and the more you've been in business. But.

Charles (:

Yeah.

Can

you, can you, for sure, can you circumvent expertise as well? Because that's one that kind of points out to me as being more difficult.

Seth Jenson (:

It can be earned, right?

Yeah, that's such a good question. That's one of my nerdy areas of the philosophy of expertise, so to speak. But the short answer is, yeah, you can definitely rush expertise. And that's often the traditional tech startup playbook is go interview tons of customers, go immerse yourself in an industry, go find those pain points and kind of master them.

And if you're really dedicated to solving a problem like that, it totally is something you can download quickly, so to speak. That being said, of course, it's easier if you've accumulated it over time, right? And there's probably a richer depth to it. But really the reality is that most people go throughout their day and just kind of live their life. They're not hunting for problems to solve. They're not hunting for business opportunities. So if you're willing to grind for a little bit and put kind of that

scientist hat, so to speak, and like really go deep on an issue, it doesn't necessarily take all that much time. You can go really far fast, but you do have to understand that like at the end of the day, expertise is a requirement. So you can't just be superficial about it.

Charles (:

No, that makes a lot of sense. And you know, it's, interesting too, cause I've worked in corporate America before and I've seen a lot of people who are accountants, right? That was my field. who are significantly older than me and they know a lot of information, but they, they don't know a lot of practical information. Sometimes, they can tell you a lot about a specific company or a inventory system, but they can't tell you.

Seth Jenson (:

Yeah.

Charles (:

how to run a small business. And so when I started my firm, I found that there was a huge learning curve for myself, ⁓ but not what I would consider the hard expertise, right? So like I had never myself clicked send on a tax return because we always had an admin doing that, which isn't a hard thing to do, right? Like it took me about five minutes to figure out in a Google search and I was done.

Seth Jenson (:

Right?

yeah, yeah, Uh-huh.

Charles (:

But pressing send that first time was terrifying. was like, did the IRS actually get it? But it's kind of an interesting point too.

Seth Jenson (:

Yeah, yeah, Uh-huh. That's amazing. But...

And that's, I feel like that's actually really important to realize is because I think a lot of people, when they're trying to decide whether entrepreneurship is right for them, they think about all the things they don't know. And that keeps them from wanting to start. And the reality is there is not an entrepreneur on the planet that knows everything they need to know day one, right? I don't care if you're Elon Musk. I don't care if you're the guy down the street starting a restaurant, like any type of entrepreneur.

there was only a fraction at the offset. can't know everything to know about accounting and you can't know everything to know about financing and you can't know everything to know about sales and brick and mortar and you the list goes on and on and on. So instead you just have to have a willingness to learn and you do want to have when we talk about expertise, it's really about the value you're providing for customers. That's what we mean first and foremost. So you and your accounting firm, you know how to manage the books of your clients in ways that are going to help their businesses thrive.

That's your core expertise. The rest you can learn. You can learn how to set up your legal entity. You already knew that as well. But for someone that didn't, those types of things, you can learn the other little, the context to what you need in the business. But you've got to know, your expertise needs to be in the value you're providing to your customers. Because that can't be faked.

Charles (:

Right.

Mm-hmm.

Seth Jenson (:

you've really got to know how to make your customers happy. And then you can learn the minutia and the logistics by trying, by problem solving.

Charles (:

No, that's a great way of explaining

expertise too, right? Cause it's a lot more than just knowing the basics of a thing or knowing what you need to get done. It's really knowing how to do a certain task or service for people.

Seth Jenson (:

Yeah, yeah. And go ahead.

Charles (:

And then the last one is financial

slack. And I think we'll probably talk about this quite a bit because this is my area of expertise. but I actually think you talked about forties and fifties as a, as a time for that financial slack. I actually think personally that it's the other way. It's the twenties, early thirties, before families, before you're settled. Boy, it seems like that's an easy opportunity. If you're thinking about entrepreneurship to use.

Seth Jenson (:

Mm-hmm.

Right.

Charles (:

then.

Seth Jenson (:

It's true. And since you're earlier in your career, there's less opportunity cost, right? So if you're in your forties and fifties, the plunge means, man, I've had 20 years of salary increases that now I'm leaving to the side versus if you're in your twenties and thirties, they're still paying you peanuts. And so it's like the opportunity cost is not nearly as high. But I think what's really important to remember is that you might not make money for a little bit, right? Like, you know, it's hard to...

jump straight out of a paying job and instantly replace your income, right? So you do need to understand the implications of that and have a really clear-eyed view of the path you're taking and how quickly you can get to cashflow. I'm curious to hear your expectations and journey when you started your firm because you had a really safe and healthy salary. How long did you think it was gonna take you to kind of build up that financial stability?

versus how much it actually took you.

Charles (:

Yeah. So it, it's interesting, right? I think a lot of people say like a goal number that is what you're trying to aim for. and for some people that's replacing their salary, a hundred percent for me, that wasn't, because I, I like being on my own.

But I think it's interesting for me, my expectations was this year, the first year of my business, that I probably wouldn't make enough. And so I had set that expectation going in. And then a lot of it was...

trying to figure out what it would take to get to the number that was safe and how long that would take. And lucky for me, my wife works and we were pretty safe at the time. So it wasn't, it didn't feel risky. ⁓

Seth Jenson (:

You could have

a longer runway than some, right? Because you had that dual income.

Charles (:

Yeah,

yeah, which, really helped. Cause I talk with a lot of friends who are starting their accounting firms and they are terrified because they're the sole breadwinner for their house. ⁓ and they can't just give that up. something else interesting too, is going back to your point, you were talking about how when you

Seth Jenson (:

Mm-hmm.

Charles (:

make too much money, it's harder to leave in some ways because it's harder to replace that. And that was part of my calculation because I said, if I'm at my company another two years, I'm to be earning another $40,000 and then it's not worth it to leave and start my own thing.

Seth Jenson (:

Yeah,

so you're like, I gotta pull the plug now, yeah.

Charles (:

Yeah. So I knew for sure. Like if, if I'm going to pull the plug and do my own thing that I needed to do it sooner rather than later, because of that kind of calculation. And I mean, entrepreneurship, you can make significantly more money. It's not like, you're limited, but I mean, standard of living creep is a real thing as you kind of get older, you kind of get used to more money and it's harder to.

break away from that and that's harder to cut that budget. And that's why I mentioned financial slack for 20 year olds. Cause boy, if I'm, if I made my first year, what I did in my twenties, I would have been totally fine. In fact, I probably would have been making more my first year than I did in my twenties.

Seth Jenson (:

Yeah. Well, and it's again, the financial context is important and it can cut both ways, right? It can be a reason to, can make it, making the entrepreneurship jump harder. It can make it easier. Like for our family, we're looking at if we're ever going to afford a home. And this really applies to anywhere in the U S right now. You almost need a side income, right? And so there's a lot of momentum or a lot of impetus for me to build up my consulting practice.

because I have a six figure salary and an amazing job that I love, but the homes around me are selling for easily seven figures. And so it's one of those things where if we want to own a home quicker, I need to build out my consulting practice. so anyway, long story short,

The important thing here is to be clear-eyed, right? And not enough people do the calculation that you did when starting your accounting firm of, okay, well, what is the timeframe? How long will it take me? How quickly do I think I can get clients or sell widgets so that I am breaking even? And how long until I'm able to pay myself a salary that that's gonna be satisfactory for my family? And so the main takeaway here is do that calculation. Look at how much you've saved and how long that can cover you. Look out.

the time it's gonna take you to break even and the time it's gonna take you to reach a salary that's gonna be sustainable. And on this podcast, we're gonna have future episodes, I think, where we really go deep into that and break down that calculation because there's some nuances there. But even if you just start with the back of the napkin, your best guess, it's worth doing, right? Because that's gonna be really influential in your decision and timing of your decision to take the plunge.

Charles (:

Yeah.

Yeah. And, back of the napkin is never perfect, but boy, think majority of my math is back of the napkin. even, even for when I'm talking with clients and things, right. Cause we need quick numbers and usually it's within five grand, 10 grand of the actual result. so take the time, figure out how much money's coming in, how much money's going out, how much you can live on. and if that means cutting certain things, then do it. and that was a conversation I had with my wife too, right? Like.

Hey, over the next year, we're going to have to be a little bit thinner on our budget. And she was on board with that because we both saw the opportunity and the long-term financial freedom and just freedom of, of time in general.

Seth Jenson (:

Yeah. And what I love about what you said there, well, A, it was a conversation with the stakeholders in your family, right? This wasn't just a, and you know, whether you're single or married or in a relationship of any kind, right? You're usually not in isolation. And so having that conversation is important. The other thing I love, how you talked about the purpose of these back of the napkin calculations and the forecast.

Charles (:

Yeah.

Seth Jenson (:

And what I'm always trying to get the people I'm training or mentoring to understand is that the power of a forecast or a calculation like this is to get you thinking about the variables that matter, right? It's to help you think through the reasoning of happening, right? Because that helps you feel more confident in your decision. You know what's gonna matter and what's not. You know, okay.

my savings matter and this is what they're gonna do for me. My revenue really matters and how quickly it comes. Do I have a sales process in play here? Like it forces you to think through the fundamentals of your business. We don't expect you to have the answers, right? These are guesses, right? You don't know how much you're actually gonna charge until you charge it. You don't know how quickly customers are gonna come until you try to get them. But it forces you to think about these things from the offset instead of just kind of blindly.

jumping in and experiencing it. I'm curious, we'll go ahead.

Charles (:

Yeah, so,

yeah, go for it.

Seth Jenson (:

So personality comes up in this conversation a lot of like who should and shouldn't do entrepreneurship. We grew up together. We've known each other since we were kids. We have very different personalities and we've both done a lot of entrepreneurship in our life. I'm curious, from, did you, were you worried at all that personality was gonna be a factor in your path?

Charles (:

Yes, absolutely. I am not the most fun and energetic person in the world. I'm an accountant. I'm an accountant. I'd like to think so. I think I'm pretty fun, for sure, I'm not your typical, when you think of entrepreneurship, you think of the people that are hustling out there that are constantly talking.

Seth Jenson (:

You're fun, Charlie. That's true, you are an accountant, but you're a fun accountant.

Charles (:

fast talking, maybe has some negative connotations too, but I'm just not that. And I'm super risk averse. You had mentioned something funny when we had talked about this podcast on taking a poll, I think of our friends when we were younger, who would you expect to be an entrepreneur? I think I would have ranked dead last and probably working at Dover Government job. ⁓ 100%.

Seth Jenson (:

And you would have said that yourself, you know? That's ⁓ not

even just other people's perception of you. Like, you would have never dreamed in a million years, I think.

Charles (:

I 100 % think that's true. And we talked earlier.

Boy, I'm not sure if it was in this podcast or previously, but one of the first things I did when I started my company is I talked to two different people and I got two different referrals. And if I hadn't, if that hadn't happened, I don't think I would be an entrepreneur. ⁓ because that gave me.

Seth Jenson (:

That's so interesting. Because it showed you

how it was possible, right? Like you're like, wait, this is, this can happen. This isn't theory anymore.

Charles (:

Yeah.

Yeah, I didn't do any hard selling. didn't, boy, just said, this is a possibility I'm thinking about. What do you think? one was to an entrepreneur, who I respected. then, one was someone who had worked in corporate for forever. and it's just interesting that both were like, I know someone that could use your help. ⁓ and that's, that was kind of what I think tilted me from.

Seth Jenson (:

Yeah.

Charles (:

This isn't just a theory, but this can be a reality.

Seth Jenson (:

Yeah, I, one of the reasons I was so excited to do this podcast with you is because again, we've been amazing friends since, I don't know how old were when we met? Like, yeah, yeah, like right before middle school or something. And again, we have very different personalities and yet our

Charles (:

11, 10, somewhere around there.

Seth Jenson (:

our paths have crossed so much. And I think it really speaks to this idea, because I am one of those sales people, right? Like I did door-to-door sales to pay for my education and I was a top rep within like instantly. I was very good at it. It paid for my, all my grad school. It came very naturally to me. I like people. I've always been very extroverted. I'm kind of that wheeler and dealer personality that is kind of the stereotype. And yet, you know,

In some ways you're more of an entrepreneur than I am really. Like you've taken that plunge. know, I've got one foot in entrepreneurship and one foot in my more corporate job. I'm very entrepreneurial. But, but, and to be fair, my corporate job is all entrepreneurship all day. So I get to have my cake and eat it too. but, but I think that really goes to show that there isn't a personality that is better suited to entrepreneurship.

Charles (:

Yeah, you have a government job. don't, I don't.

Seth Jenson (:

Some of the best entrepreneurs in the world are, you know, every spectrum in terms of neurodivergence, they're every introvert to extrovert, they're every culture, you know, is represented. Although that isn't interesting. There's a lot of research into the culture thing and culture does matter. But all that's to say any personality can be a good entrepreneur, but they do need to be willing to do certain things. And some personalities and cultures are less willing to do certain things.

So really I'd say, don't fret about your natural inclination, so to speak, in terms of, again, how gregarious you might be or not, or whether you identify with that hustle culture. That's not actually that important to me at all. What is important is, are you willing to sell? Because unfortunately every entrepreneur does need to sell. Now that doesn't mean they have to be salesy.

and we'll talk more about that in the future, but you do need to be willing to put yourself out there and let the world know about what you're offering. You need to be a good communicator through and through as you get employees, with clients, with partners. It's a lot of communicating. You're really just organizing value in the community and that takes a lot of working with a of people. You have to be willing to work more than you want to because entrepreneurship will just...

eat away at your time no matter what venture it is, whether it's venture-backed tech or whether it's again a food truck, it doesn't matter. It'll try to steal all the time out of your day. I think really one of the best metaphors is having a kid. Entrepreneurship is like having another child in your life because they're needy and it's going to want to take up all your time and attention, but it's worth it. I believe having kids is worth it as well. I'm very grateful I have one.

So then, so you have to be willing to sell and communicate. You have to be willing to work more than you want to, to make this survive. And you also need to be willing to experience a lot of ambiguity in your life. And this is not going to be handed to you. The pathway has to be made. And so you have to be willing to organize and act despite knowing the outcomes and having to form the outcomes you're looking for out of.

the ether, to speak. those are maybe three rather than four, sell and communicate, work more than you want to and deal with ambiguity. But if you've got those three things, I don't care whether you're the most introverted or expert person in the world, you can do it.

Seth Jenson (:

One other thought I had about the personality question is there's been a lot of fun research about people that have experiences with the world that society might say is disordered or a disadvantage, and they end up thriving in entrepreneurship. the two that come to mind, there's been some really cool research on it, is people with dyslexia, for example, are like,

way overrepresented in entrepreneurs. Again, there's lots of different ways why we think that might happen. It could be because they weren't, I remember that from growing up and stuff. ⁓ And again, it's hard to say exactly what the mechanisms are here, but yeah, if you take an entrepreneur, the odds of them being dyslexic are like way higher than the national average. And it could be because school sucks for people that are dyslexic, our current system.

Charles (:

Did you know I have dyslexia?

Yeah, interesting.

Seth Jenson (:

And so they're forced to learn other schools to like kind of adapt other skills at school rather. And so they learn how to be more independent or, or, you know, people's skills. But, know, again, the it's, I don't want to pretend we know exactly the causal mechanism there. other thing is often people that are obsessive or, you know, they're find a place for their ADHD or, you know, the kind of those hyper-focused people.

which again can be hard in the classroom context when you're switching and giving tasks you have no interest in and things like that. It's hard to be someone with ADHD in that environment. Well, it turns out it can be a great place for an entrepreneur. Many of my closest friends that have built just mind blowing businesses are crazy ADHD, like the most like textbook case you can imagine. And it ends up being a superpower for them. I love that about entrepreneurship that like

You can be really boring like me and normal, like very like average in every way, or you can have a very different experience from everyone else. And entrepreneurship has the flexibility to help you thrive in that space. I love that about that. And I think it speaks to the potential of entrepreneurship and the fact that really all personalities are welcome in this space.

Charles (:

Yeah, going through it, you were talking about selling, communicating, work more than you want and experience ambiguity. That's kind of like your, your three to four main points of what you're expecting. None of those to me strike me as, like you don't have to be an extrovert or you don't have to be the smartest person that ever existed. Right? Like you can be a normal everyday person and make this work. You just have to be willing to try.

Seth Jenson (:

Yeah, absolutely.

And we'll, think we really should have a whole episode on sales because that's the one that get people get hung up on and think, I have to be a certain type of person to sell. your, example, you know, shows how wrong that is. Right? Like the first two conversations you have end up becoming sales opportunities that you weren't even asking for, but, just putting yourself out there, trying to create value in the marketplace, the sales happened and you were being genuine and, and, people were finding you. So,

Charles (:

Yeah.

Seth Jenson (:

it don't let that one hang you up because anybody can sell.

Charles (:

Yeah. And I think too, we all sell all the time. think what did it for me is I know people need accounting. People need tax work. They need bookkeeping for their businesses. So it was really easy to be like, well, I'm offering this service. You're welcome to take it. Like, and it's not personal for me. and I'm just giving them the chance. And so for me, it was a really easy sell, because of that.

Seth Jenson (:

Yeah.

Charles (:

Cause I framed it in my own mind as, I'm giving a service that they need. They're already going to buy this somewhere. why can't it be me? And so I'll just, I'll offer it. And if they say no, that's fine. Like, it's hard to not make it personal, I think sometimes, but if we can do that, it really is a pretty easy job.

Seth Jenson (:

Yeah, for sure. And one other kind of factor that I think plays into that discussion about whether you as a, you know, your personality or the way you live your life is a good fit for entrepreneurship. With the digital and AI revolutions we're experiencing, it offers more flexibility in what entrepreneurship looks like as well, which I think is fascinating where, ⁓ you know, before

Charles (:

How so? ⁓

Seth Jenson (:

Yeah. So like, you know, if I was starting a company in my parents' generation, it would be a lot of more in-person experiences, right? Like, and your marketing would be billboards and these different things. Today, with a couple of AI assistants and systems in place, you can build an entire company from your desk and go through growth stages with being your only employee. And there's just so much.

power in the digital marketplaces that have been built and the AI systems that are now supporting the entrepreneurial process, that it's kind of breaking the rules of what entrepreneurship is. And I think widening even more the opportunities of who it's a good fit for. Again, it's too early to tell exactly how that's going to play out, but it's definitely opening the world even more than before. I think the opportunities are...

Charles (:

Interesting.

Well,

and I have a client, right, who's making a million dollars, works from home, is the only employee. I think they just got a VA, but like, that's a pretty low bar. That's really low overhead. It's really simple to do. Obviously it's not gonna be for everyone. I don't know enough about AI and the online world to be able to do that myself, but I know a lot of people do.

Seth Jenson (:

huge.

Yeah.

Yeah, and like anything in entrepreneurship, it's a skill you could learn, right? And maybe we'll all be forced to, right? Like in some sense. ⁓ But you don't even need to. Yeah. And it used to be like, entrepreneurs, they're like the leaders of men and all these different things. It's like, no, you can just be like a homebody crushing it with your new business if that's kind of, you know, how you want to live your life.

Charles (:

Yeah. Well, I am learning AI quite a bit. Yeah.

Yeah.

So something that I think this brings up and we've talked about kind of what personalities you need. We talked a little bit about, making sure we have enough money and we have expertise and we have a network that we can kind of build on. How do you force yourself to go from that? Like I've got this expertise, I have a network and I have some financial flexibility.

I'm totally willing to sell and communicate. How do we make that next step then to actually starting the business?

Seth Jenson (:

Yeah, so for me it really starts with goals. I think you have to know exactly where you wanna go so that you can choose the path that's most appropriate to it, right? And so there's a lot of reasons to get into entrepreneurship and I think we're gonna do a whole episode on those reasons, the motivation.

but you wanna understand what they are for you. If you're financially minded and you're like, really the reason I'm starting this business is so that I can be a multimillionaire, that's awesome. That's great, let's go for it. But you need to understand what paths are gonna...

yield those types of results. If it's, hey, I just want to match my current income and have more flexibility over my time, that's great. But you've got to understand, okay, what path is going to get me there? So having really clear goals and expectations and the best goals, again, we could talk about smart goals, blah, blah, blah. The most important thing is that they're not vague, They've got to, numbers are your friend, right? Like get numbers because that'll force you to reverse engineer the path to get there.

Charles (:

Everyone's heard it.

Seth Jenson (:

If you wanna have a multimillion dollar business, you need to have products that sell at margins and in quantities that are gonna get you to multimillions, right? This is not a, it's not a food truck. I'm sorry. That's not gonna be your pathway to multimillion dollar companies. Yeah, if you're Chipotle, then.

Charles (:

but a fleet of food trucks, now we're talking. But you can, and that's

what I think is really cool about entrepreneurship in general is you can set those goals up and then work backwards from there and really figure out what you can do to get there. And I'm sure you've seen it too, but something that was I think the most shocking to me is that you can, there are tons and tons of really good businesses out there and it doesn't so matter

what you're doing, right? It can be a plumbing, can be lawn care, it can be marketing, it could be accounting. ⁓ And you can make those millions. It's really more of how you set yourself up to get to that point.

Seth Jenson (:

Absolutely.

Absolutely. No, again, we love the concept of unsexy entrepreneurship because like there are secret hundred, you know, you know, people just rolling in revenue all around you and they're doing concrete businesses or fencing businesses. Like there's some gravel pits near where I live and turns out gravel.

Charles (:

you

Seth Jenson (:

is the game to be in. It's like you wouldn't, you'd be just shocked. So yeah, it's find that path that works for you, something that you're willing to go the long haul in, right? Because this is, it's like having a child. Like you can't just leave it, right? This is a long process that it's gonna need to mature and grow.

Charles (:

It sells.

Mm-hmm.

Seth Jenson (:

you're gonna have to be an expert in it like we talked. These people are gonna be your people, your clients and your partners. So choose a path that's gonna get you where you wanna go, that you've got those very specific goals and you're like, yes, I can see a way that this grows into what I needed to be. And then the second question to ask yourself is like, do I wanna be in this relationship with this business? Like, do I like our dynamic? Am I passionate or interested in this space enough?

to go for it because it's going to be all you think about for a really long time. ⁓

Charles (:

Yeah.

And then on the other side of it, right? Like we talked about the a hundred million dollar goal. I have another person. know that they're the opposite side. They're like, I want to work 15 hours a week. Uh, and they've, they make a quarter million dollars a year and that's hard to argue with. Um, and you know, yeah, yeah. And so I think it's really cool that you can set up all these different types. Uh, and some things I think are easier than others. Uh, like I don't think.

Seth Jenson (:

Sounds like a great path. ⁓

Charles (:

path she's going on.

she would have to work, well, not every career or every job would be able to do that. She's in a very specialized field, right, so she can offer that. So like a lawn care, if you're gonna work 15 hours a week, you'd have to really, really, really scale to get to that point of working only 15 hours a week would be my guess. But these are all important things to realize. it's still doable, yeah.

Seth Jenson (:

but it's doable, right?

because even those very hand-to-hand businesses like lawn care, for example, that's a great example. Like you say, at a certain scale, you are able to eventually walk away from it and it runs itself and things like that. that is a lot, the journey to that tends to be much longer than most people want. You usually go in, know, bright-eyed and bushy-tailed.

Charles (:

Five years.

Seth Jenson (:

And you find out that it's a much longer path than you wish it is, but it's doable. If you stay on that path that you'll get there. And in terms of timeframes and goals, I usually encourage people to think in two to three year timeframes because anything worth building typically takes that long to really get off the ground. There are exceptions. I have good friends who built their business. They started in September of 2024.

And by December of:

Charles (:

wow.

Seth Jenson (:

Those are exceptions that usually think in terms of two to three years of building and getting somewhere that's really going to be cooking, building up that client base, the suppliers, whatever it might be. By the way, I feel like we reference service businesses a lot because you're a service professional. My consulting practice is obviously service-based, but the principles are the same. The pathways are very different, whether you're doing something like an e-commerce or physical goods.

a CPG or service-based business. But in either cases, give yourself two to three years. Services usually get off the ground a little faster because in your case, like you said, even before you started, you had two clients lined up. You can kind of just go provide that service out the gate. Yeah.

Charles (:

Yeah. Well, and low overhead too in services. But I mean,

I'm sure we'll talk about margins and things like that later. But service businesses, I think can be harder to scale in some ways than manufacturing and retail and restaurants for that matter. ⁓ It can be easier, can be harder. They're pros and cons to every business. ⁓ But I do think service based businesses are easier to start and get going with.

Seth Jenson (:

Yeah, absolutely.

Mm-hmm.

So, and that's why I say those two to three years are really for you to gut check yourself and be like, it could take me two to three years. Am I ready for that? Right? Because it hopefully takes you two to three months. Like don't let that limit you. Be those entrepreneurs that, you know, in your case, I think within six months, you'd built up your practice to the point where you had a great salary that you're already able to pay yourself. Right? And that's, that's half a year.

Charles (:

Yeah.

Seth Jenson (:

But you were ready to go the long haul, right? Like you had accepted the fact it could take you much longer than that. And that's critical because for many, does take longer. And many times there's multiple pivots. start in one business and then you basically have an entirely different business 12 months later. And so you've got to give yourself a room.

Charles (:

Well, so

let's talk about this because for me, I planned on 12 months. I know a lot of people that I've talked to have planned for longer or shorter periods of time. How do you know what you can accomplish?

Seth Jenson (:

So you don't, that's the beauty of entrepreneurship, right? The only guarantees I can give you is if you persist, you can get there, right? I don't care how big your goal is or how crazy it is, there is a pathway to do it. And I know that because other people just like you have done it, right? If your goal is to be the first, you know, multi-trillionaire, okay, you're gonna be a trailblazer, I can't tell you how to do that, asteroid mining or whatever.

Charles (:

You

Mm.

Yeah.

Seth Jenson (:

But if your goal is to be a billionaire, there's a lot of people that have been successful. So you know there's a pathway. It will take a long time. The bigger that goal is, a lot of the time, the more time you're gonna have to invest in it. So I can't, there are no guarantees other than you can get there. I know people that have built businesses and it took about 10 years to get where they wanted to, you know, in the range of $50 million businesses. I know people that have gotten there in three, right?

to that same $50 million mark. So I can't tell you how long it'll take, but what I can tell you is you can get to these goals if you're willing to persist. And that speaks to kind of, think for me, like the last concept I'd really like people to understand before they take this plunge, which is in entrepreneurship, you are in control. And that's a blessing and a curse.

It means that you can make anything you want happen. It also means if you don't do it, nothing's going to happen. And so as you decide to take this path in your life, you've got to come to grips with that fact and decide whether that's the life you want to live. The nine to five offers, it puts the control in someone else's hands and it takes the responsibility off your shoulders. And there comes with all the negative things that come from that, right? You have a boss, your salary is capped, all of these different things. Entrepreneurship, you don't have that, but it also means

If you don't get out there and make it happen, then nothing happens.

Charles (:

Interesting. Do you find that most people give up because they're scared of that? Is that usually the biggest hurdle?

Seth Jenson (:

I think a lot of the types of people that are attracted to entrepreneurship tend to be the people that want to maintain the locus of control. and so it, tends to be kind of a filter naturally, the people that are most interested in entrepreneurship. but I think it's kind of, that's why it's so scary is because everyone knows in the back of the mind that's happening. So my, my advice is to embrace it. Be like, you know what? Like instead, like look, face it front, you know, head on.

and say, I'm in control. I have to make things happen and I will make things happen. And then say, and I'm going to go all out. That's why people always say to go all out. It's for this concept. Like let's give it everything you have for 12 months, even six months. That's enough to get really deep into something. Because until you really assume that responsibility, you won't know. You won't know what it feels like and you might love it.

You might hate it, and that's okay too, but you'll only know by going all in and really going for it.

Charles (:

Yeah, no, I think that's really true. And something kind of a stop gap for myself was it was always I can go find another job, which was true and still is. There's a huge shortage of accountants, which made me feel really confident in making my jump. But it was pretty quick. I I love being in control, which is maybe a downside and a positive at some points.

Seth Jenson (:

Yeah.

Heh.

Charles (:

that ownership I just loved. It just fit me so well.

Seth Jenson (:

Yeah.

I'm the same way. I did my internship in university, you know, I was a finance major, so you have to go do an internship. I hated it. I hated it. I didn't want my job. I didn't want my boss's job. I didn't want my boss's boss's job. Like it was so clearly because of that.

someone just telling me what to do and sit at my desk for a certain amount of time, right? It's why I did academics, because you have, at least I thought you have a lot more control. Turns out you don't have as much as you think you do. And yeah, it is a magical feeling. And I think most people will realize that they love it, but it's not for everybody. And there's nothing wrong with that career path. And I think when you think about the opportunity cost,

Charles (:

Yeah.

you

Seth Jenson (:

Remember that building a business is almost always harder than getting a great job. All the skills it takes to build a business from the ground up or to take over a company through acquisition, all that work and skill set could be applied to getting a great job. And it's much more likely to be successful in a shorter time period at getting that great job, right? The networking, the creating value, all of those skill sets.

Charles (:

Mm.

Seth Jenson (:

can be used to get a great job. And for many people, that's a great path for them, especially people that are really in a financially difficult situation. ⁓ Just know that that's a path for you, right? I like to create my own jobs. Every time I've had a corporate job, it's because I've created it for myself. And that's a pathway you can have, right? There's businesses that want people to be entrepreneurial within their organization. And so just know that that is a path that is great as well.

Charles (:

Mm.

Seth Jenson (:

And ⁓ it's certainly not harder than building something from scratch or taking over an existing business.

Charles (:

Yeah.

Yeah, it's a lot easier to get a job, I think. And I think, well, I mean, from my perspective, right, I have to keep and maintain quite a few clients, dozens of clients. I have to keep them happy, well maintained, constant communication with all of them. That's a lot harder to manage than just my boss, just the CFO of a company, right? Like that's easy.

It's one, one person to reach out to only have to prioritize one thing. but boy, I personally, I love entrepreneurship. and I'm so excited as we keep talking about this, I keep telling Seth, is my, my version of an MBA program, cause I'm never going to go back and get one. so I'm excited to talk.

Seth Jenson (:

Well, I don't believe in MBA programs, so this podcast is much

better than an MBA. I've taught a lot of MBA students. ⁓ Good choice, Charlie, good choice.

Charles (:

You

Awesome.

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About the Podcast

Unsexy Entrepreneurship
How to Start, Acquire or Grow Your Business.
Want to quit your job and build real financial freedom—but not sure where to start?

This podcast is for millennial entrepreneurs who are ready to take control of their future through business ownership. Whether you’re looking to start a business, buy an existing business, or grow a side hustle into a full-time gig, we give you the real-world playbook that actually works.

Hosted by Charles Harris, a CPA turned business owner, and Dr. Seth Jenson, director of The Entrepreneurship Institute and an Oxford PhD in Business Strategy who’s helped thousands launch companies, this show cuts through the noise and gives you straight talk on:
• How to start a business from scratch
• What to look for when buying a small business
• The mindset shift from employee to entrepreneur
• How to avoid beginner mistakes that cost you time and money
• Proven strategies to grow your small business

No fluff. No hype. Just the unsexy truth about building a business that works—so you can build a life you actually want.

Subscribe now if you’re ready to stop dreaming and start doing.

Got questions? Contact us here: https://tinyurl.com/6fwvem3v

About your hosts

Charles Harris

Profile picture for Charles Harris

Ian Martin

Profile picture for Ian Martin
Producer, Audio Engineer, and Founder of TheAudioMarketers.com